5-fluoro-2-[(3-methylbut-2-en-1-yl)oxy]benzaldehyde | 1013098-84-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-fluoro-2-[(3-methylbut-2-en-1-yl)oxy]benzaldehyde
• 英文别名: 5-Fluoro-2-(3-methylbut-2-enoxy)benzaldehyde；5-fluoro-2-(3-methylbut-2-enoxy)benzaldehyde
• CAS: 1013098-84-4
• 化学式: C₁₂H₁₃FO₂
• 分子量: 208.232
• InChiKey: WMVHAHCFIUBSHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-fluoro-2-[(3-methylbut-2-en-1-yl)oxy]benzaldehyde 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正庚烷 、 二氯甲烷 为溶剂， 反应 1.67h， 生成 hexacarbonyl[1-{5-fluoro-2-[(3-methylbut-2-en-1yl)oxy]phenyl}-3-N-Boc-methylaminoprop-2-yn-ol]dicobalt
  参考文献：
  名称：

  A highly diastereoselective series of Nicholas cyclisation reactions of N-Boc-protected propargylamines

  摘要：

  The reaction of N-Boc-protected propargylamine with salicylaldehyde derivatives and their subsequent Nicholas cyclisation reaction to provide a range of novel benzopyrans is reported. The cyclisation reactions proceeded with excellent levels of diastereoselectivity to afford compounds with cis-relative stereochemistry. As far as we are able to ascertain these are the first reported examples of Nicholas cyclisation reactions of propargyl alcohols that bear a terminal alkynyl N-protected amino motif. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.08.087
• 作为产物：
  描述：

  5-氟水杨醛 、 1-溴-3-甲基-2-丁烯 在 potassium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 以82%的产率得到5-fluoro-2-[(3-methylbut-2-en-1-yl)oxy]benzaldehyde
  参考文献：
  名称：

  A highly diastereoselective series of Nicholas cyclisation reactions of N-Boc-protected propargylamines

  摘要：

  The reaction of N-Boc-protected propargylamine with salicylaldehyde derivatives and their subsequent Nicholas cyclisation reaction to provide a range of novel benzopyrans is reported. The cyclisation reactions proceeded with excellent levels of diastereoselectivity to afford compounds with cis-relative stereochemistry. As far as we are able to ascertain these are the first reported examples of Nicholas cyclisation reactions of propargyl alcohols that bear a terminal alkynyl N-protected amino motif. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.08.087

文献信息

• In situ mechanochemical synthesis of nitrones followed by 1,3-dipolar cycloaddition: a catalyst-free, “green” route to cis-fused chromano[4,3-c]isoxazoles
  作者：Zigmee T. Bhutia、Geethika P.、Anurag Malik、Vikash Kumar、Amrita Chatterjee、Biswajit Gopal Roy、Mainak Banerjee

  DOI：10.1039/c5ra21044e

  日期：——

  An efficient, catalyst free mechanochemical route to cis-fused chromano[4,3-c]isoxazoles has been developed via a simple mortar-pestle grinding method.

  一种高效、无催化剂的机械化学途径被开发出来，通过简单的研钵研磨方法合成了cis-融合的色葡萄糖[4,3-c]异噁唑。
• The synthesis and biological evaluation of a range of novel functionalised benzopyrans as potential potassium channel activators
  作者：Elizabeth Tyrrell、Kibur Hunie Tesfa、Iain Greenwood、Alistair Mann

  DOI：10.1016/j.bmcl.2007.11.135

  日期：2008.2

  A range of novel benzopyrans have been synthesised and biologically evaluated for K-ATP channel activity employing cromakalim 1 as a benchmark K-ATP channel opener. Although the compounds that were evaluated demonstrated a reduced ability to relax phenylephrine stimulated rat thoracic tissue, we provide evidence that benzopyrans 7a-h may be operating via an alternative mechanism than ATP-sensitive K+ channel activity. (C) 2008 Published by Elsevier Ltd.
• A highly diastereoselective series of Nicholas cyclisation reactions of N-Boc-protected propargylamines
  作者：Peter Brawn、Elizabeth Tyrrell、Mark Carew、Kibur Hunie Tesfa、Iain Greenwood

  DOI：10.1016/j.tet.2012.08.087

  日期：2012.12

  The reaction of N-Boc-protected propargylamine with salicylaldehyde derivatives and their subsequent Nicholas cyclisation reaction to provide a range of novel benzopyrans is reported. The cyclisation reactions proceeded with excellent levels of diastereoselectivity to afford compounds with cis-relative stereochemistry. As far as we are able to ascertain these are the first reported examples of Nicholas cyclisation reactions of propargyl alcohols that bear a terminal alkynyl N-protected amino motif. (C) 2012 Elsevier Ltd. All rights reserved.